The vicious cycle of early stage capital — or lack thereof – Portland Oregon startups, tech, news, events, jobs, and community Not a week goes by that I don’t have this conversation with a local founder. “Why is it so hard to raise early stage capital in Oregon…?” or “Why is there so much risk avers…

I talk about this all of the time. Like weekly. So I finally wrote it down. For posterity. Or for sharing or whatever. So if you've ever found yourself asking, "Why isn't there more risk tolerant early stage capital in Oregon…?" this is my response.
siliconflorist.com/2026/04/22/t...

I read this as a threat “They’re going to grumble that we are interfering with their business model and, instead of holding them accountable, we should be doling out public dollars to incentivize them to get more money,” Dunphy says. “But I’m deeply disinterested.”

The study isn’t being done on solving for vacancy. The study is about what impact the tax might have. Imagine if councilors would have started all this with sitting down with some property owners to learn more about the situation they find themselves in. Could have saved us $70,000

Would a Vacancy Tax Spur Owners of Empty Towers to Seek Out Commercial Tenants? To reduce blight and revitalize downtown, a trio of progressive councilors wants to explore penalizing owners of long-vacant commercial and retail properties.

I can’t imagine paying your property taxes and doing everything you can to find tenants only to have elected leaders threaten you with a new tax without ever discussing with you 😔

www.wweek.com/news/2026/04...

🤣🤣🤣🫣🫣🫣

Duck that guy 😒

Black History Month 2026: A recap of Pitch Black participants – Portland Oregon startups, tech, news, events, jobs, and community Every February, Stephen Green celebrates a series of amazing folks for Black History Month by posting one post a day for the entire month. This year, he focused his efforts on folks who participate…

It's a Black History Month tradition. @pdxstepheng.bsky.social shares one profile per day throughout February, and then I gather them all up into a single post for future reference. This time around, it's a Pitch Black alum edition. siliconflorist.com/2026/03/02/b...

A PSA for you to share if you’re getting the “Are you okay? Is it safe there?” sorts of queries: Portland Oregon is absolutely fine #pdx #portland (Footage courtesy @pdxstepheng.bsky.social)

OPB

Feeling frustrated? Go give time or money to OPB or something - protect the rare remaining independent media in your community. www.opb.org/give/

…. There’s a ton I would change about prosper and how we position economic development in the region but consistently shitting on bureaus without offering up solutions helps no one.

I think that’s the point… TIF isn’t a magic wand. I don’t think the city has ever bought into having resources that are non tif to support businesses and community. How do we start having conversations about other needed tools and put them in context of what TIF can do. That’s bigger than prosper.

There seems to be a third thing that’s as consistent as death and taxes… that’s @jamiedunphy.bsky.social shitting on Prosper Portland work while disregarding data, basic economic principles or state law. 😒

Portland City Councilor Hires, Then Immediately Fires Controversial Local Podcaster Local podcast host and video producer Andy Chandler was hired as a part-time videographer by City Councilor Dan Ryan, then fired soon afterward when Ryan’s office discovered Chandler’s public politica...

Councilor Dan Ryan's office had controversial local podcaster Andy Chandler on staff for 3 days before realizing Chandler's personal views were "not in alignment" with that of Ryan and his team. Chandler frequently platforms anti-trans guests and lambasts DEI as racial discrimination.

The latest controversy on Councilor Dan Ryan — the only current elected official who has voted against the expansion of Portland Street Response multiple times.

We believe District 2 wants to invest more in PSR and less on controversial right wing podcasters.

Stephen Green of Pitch Black on The Long Con podcast w/ Rick Turoczy

If you’re looking for something to do today, @pdxstepheng.bsky.social and I would be happy to hang with you for a bit youtu.be/ALRCxWDQx8c

So that is the thing if you have “ongoing” allocation you don’t have to ask every time. The budget defaults to including money for you. The bigger picture isn’t about Prosper it’s about whether the city wants to invest in economic development at all. This amendment ends funding for that.

Once ongoing budget goes away it doesn’t come back. At the end of the day it doesn’t have to even go to Prosper. The real question is how will the city invest in economic development moving forward? What’s the plan for making a better solution for ecdev then what we have today?

$40 million gets spent down to zero in 2-3 years with the programming that it pays for. They could do less loans to businesses or fund business assistance providers at a lower level but the money still runs out. What’s lacking is a plan for how economic development happens after the money is gone

So what happened when the money is all spent? How do we fund economic development in 2-3 years from now?

Prosper worked with the mayors office to take a 12% budget cut as part of his budget. They were already taking a cut. This amendment ends ALL of their future funding from the general fund

Details matter here. They are ending ongoing general fund allocations and they are asking Prosper to replace that money with money that is used for a loan fund that supports small businesses. Once that money is gone in 3 years they have nothing left.

Why @councilorgreen.bsky.social & @jamiedunphy.bsky.social would be “defunding” small business in Portland with their amendment to cut all general fund money from Prosper Portland. No one in community asked them to do this and it would have catastrophic consequences.

An opportunity to support an organization that provides crucial support to the Portland startup community I’m writing to ask for your help. Our peers and the organizations that support them in the Portland startup community are in need of assistance. Why…? Newly elected Portland City Council memb…

To @councilortiffany.bsky.social so you can’t say you didn’t hear from small business owners…. We do NOT want you to DEFUND Prosper Portland. Critical funding and support to BIPOC owned businesses across #Portland would be lost.

siliconflorist.com/2025/05/18/a...

This is tax increment finance money so no this money can’t legally be used to do the work

Sorry to get technical on you but this graph doesn’t look at age of the people moving. Econorthwest work did and it was degrees folks in their 20-30s moving here

That’s actually not what census data has been saying. The folks at Econorthwest have been sharing that younger folks continue to come here

I think we should have a regional business advancement team that doesn’t force cities to compete with each other and is staffed industry professionals and business owners. We need to be finding ways to be proactive & ways to center what’s best for businesses vs. “this is what we’ve always done”

It really depends on your perspective; we have the most diverse city in our history, natural resources and the region as a whole is getting better. It’s time to lean into reimagining what Portland looks like in the changing landscape.